Synthesis of Highly Functionalized Cyclohexenone Rings: Rhodium-Catalyzed 1,3-Acyloxy Migration and Subsequent [5+1] Cycloaddition

Lead Rh‐ole: Highly substituted cyclohexenones were prepared from cyclopropyl‐substituted propargyl esters by using a [{Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3‐acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2011-02, Vol.50 (6), p.1346-1349
Main Authors: Shu, Dongxu, Li, Xiaoxun, Zhang, Min, Robichaux, Patrick J, Tang, Weiping
Format: Article
Language:English
Subjects:
carbocycle
Catalysis
cycloaddition
Cyclohexenes - chemical synthesis
Cyclohexenes - chemistry
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
rhodium
Rhodium - chemistry
ring expansion
Stereoisomerism
synthetic methods
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Summary:Lead Rh‐ole: Highly substituted cyclohexenones were prepared from cyclopropyl‐substituted propargyl esters by using a [{Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3‐acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the presence of CO with high regioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006881